Alone in the crowd, the Rev. Jesse L. Jackson watched through tears in the cool Chicago evening as the nation’s next first family took the stage: a black man named Barack, a descendant of slaves named Michelle and their two young daughters.

As in much of the country, the feeling in Grant Park on election night nearly five years ago emerged from the heady pride of progress. But for Jackson, the moment pushed him backward, through decades, to those he called “the martyrs” of a movement whose successes Obama had inherited.

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Asked where President Obama has fallen short, Rev. Jesse Jackson told Nia-Malika Henderson that Obama should revive the war on poverty and address voting rights and student loan debt while he is still in office.

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Road closures, Metro tips for March on Washington anniversary.

“I could see them coming across the stage,” Jackson said. “Those caskets we marched behind. And the people who made that night possible couldn’t afford to be there. They would be either dead or injured or poor.”

Obama’s relationship with the American civil rights movement has been a vexing one, challenging a cool, intellectual president to engage the memories and expectations of pioneers who marched, resisted and, in some cases, died before his birth.

On Wednesday, the arc of that relationship will reach from Grant Park to the steps of the Lincoln Memorial. On the spot where the Rev. Martin Luther King Jr. described his dream 50 years ago, Obama will define a new front in the fight for equality and identify the mounting threats to progress emerging today.

In preparing for the address, Obama has assembled civil rights advocates at the White House to discuss states’ efforts to make it harder to register to vote and cast ballots, nearly five decades after passage of the Voting Rights Act. He has met with religious leaders. He has phoned Rep. John Lewis, the Georgia Democrat who marched at Selma, Ala.

According to those he has spoken to, Obama will say that gay men and lesbians, women’s rights advocates, immigration activists, and African Americans must come together as a coordinated political movement to defend rights in peril, particularly at the ballot box, and to secure new ones in such areas as marriage equality and criminal sentencing.

Although those groups are at odds on some issues, the broader demand for equal treatment unites many of them in ways that the political movements of the 1950s and 1960s could not.

But King spoke as a leader outside the government, affording him a certain rebel’s freedom. Obama, as president, is searching to define his own role, constrained by his sense of race and by his responsibility to constituencies beyond King’s.

“I don’t think people want him to be the black president or speak to black issues,” said a senior administration official, who spoke on the condition of anonymity to describe Obama’s thinking about the speech and the moment it presents.

“He’s the president of the United States; he’s not a civil rights leader,” the official continued. “So his message will be far broader, directed at the country as a whole.”

Competing expectations

Obama has often declined to distinguish problems facing black communities from those confronting whites, Latinos and others, sometimes disappointing his mostly adoring African American supporters. He brushed aside the historic nature of his election early on, saying that “there was justifiable pride on the part of the country that we had taken a step to move us beyond some of the searing legacies of racial discrimination.”

“But that lasted about a day,” he added.

The remark heartened some white voters, perhaps fearful of a heavy focus from the White House on the concerns of African Americans. At the same time, black leaders have said he went too far in the other direction — ignoring race and the unique plight of black Americans.

In a Pew Research Center poll published last week, a little more than a quarter of African Americans surveyed said the prospects for blacks have improved since Obama was elected. One in five said opportunities for blacks have worsened.

“Barack came from talents, skill, temperament, and vision and preparation, and took it all the way across the goal line,” Jesse L. Jackson said. “But he ran the last year of a 54-year race. He came out of a series of struggles to keep broadening the base. Surely, because he has won, it redefines what is possible.”

It has also redefined what is expected of him, not only as a black president, but also as a black father and former black teenager.

Last month, Obama showed more inclination to speak personally about the black experience after a jury acquitted a neighborhood watch volunteer in the fatal shooting of Trayvon Martin, an unarmed 17-year-old in Florida.

In explaining many African Americans’ anger at the verdict, Obama identified a “sense that if a white male teen were involved in the same kind of scenario, that, from top to bottom, both the outcome and the aftermath might have been different.”

“When I talk to Malia and Sasha, and I listen to their friends and I see them interact,” Obama said of his daughters, “they’re better than we are — they are better than we were — on these issues. And that’s true in every community I’ve visited across the country.”

Linking two generations

Jackson belongs to what Obama has called the Moses Generation — the founding leaders of the civil rights movement. He has called his own age group the Joshua Generation, and building a link between the two has been among his chief challenges when it comes to his relationship with some civil rights leaders.

“I’m here because somebody marched. I’m here because you all sacrificed for me,” Obama told a group of leading Moses Generation members after declaring his presidential bid in 2007.

“I thank the Moses Generation,” he said. “But we’ve got to remember, now, that Joshua still had a job to do.”

Joshua DuBois, who headed Obama’s Office of Faith-Based and Neighborhood Partnerships during the first term, said the president rarely advertises the time he spends talking to Moses Generation figures.

“He’ll address the real, practical problems that the African American community and the broader community faces,” said DuBois, who plans to attend the speech Wednesday despite his wedding being scheduled just four days later. “But he’ll do it in a way that connects all Americans.”

Echoing Obama, DuBois said the “best way to highlight these issues,” whether economic inequality, gun violence or underperforming public schools, is “to extend them beyond the black community to all communities.”

At the March on Washington half a century ago, King implored his mostly black audience to embrace white Americans who shared their demand for racial equality. “For many of our white brothers, as evidenced by their presence here today, have come to realize that their destiny is tied up with our destiny,” King said.

DuBois says that passage of the speech has influenced Obama, whom he often prayed with during his time in the White House.

Valerie Jarrett, a senior adviser and longtime friend of the Obama family, said King’s appeal across racial lines inspired Obama to work on Chicago’s South Side as a community organizer, mediating between a mostly black community and a predominantly white city power structure.

“Coming out of school, he was motivated by that spirit of Dr. King’s address,” Jarrett said. “And now he’s talking to issues that disproportionately challenge African Americans right now, but they also challenge all Americans.”

Denying a stark divide?

But some Joshua Generation blacks hope to hear something else from Obama on the Mall on Wednesday — a frank appraisal that heightened racial acceptance has not resolved a lack of opportunity for many blacks.

Ashley Bell, a former county commissioner in Georgia, voted for Obama in 2008. He plans to travel Wednesday with his 14-year-old daughter to the Mall to hear Obama, even though he voted for Republican nominee Mitt Romney last fall.

“Many of us in America may criticize his policies, but we also understand in this country that our politics is beyond color, in the way that 50 years ago it was not,” Bell said. “But we can’t get caught up in the symbolism of having a black president, because it has not broadly improved the situation of black Americans. There must not just be civil justice, but economic justice.”

In May, speaking at Morehouse College in Atlanta, King’s alma mater, Obama told the graduating class, “My job, as president, is to advocate for policies that generate more opportunity for everybody.”

“Those are matters of public policy,” he said, “and it is important for all of us — black, white and brown — to advocate for an America where everybody has got a shot in life, not just some.”

That speech, cited by Jackson as a milestone in presidential leadership on civil rights, was a candid acknowledgment of racial inequality and the responsibility of white America to remedy the imbalance. He called the lack of opportunities for blacks an “American failure.”

“For Negro poverty is not white poverty,” Johnson said of racial differences. “For the Negro they are a constant reminder of oppression. For the white they are a constant reminder of guilt. But they must be faced, and they must be dealt with, and they must be overcome.”

Nearly five decades later, rates of unemployment, graduation and incarceration remain worse among blacks relative to their share of the population. Jackson said in a recent interview, “The racial separation has closed, and disparity has intensified and increased.”

“So, we’ve got the dream, but we need the budget,” he continued. “And that’s what the president has that no one else can offer.”

‘He has his voice’

Obama has not ignored black America. He has pushed for new restrictions on gun sales as a way to combat violence and advocated for more money and accountability to improve urban schools. Three years ago, he signed the Fair Sentencing Act.

But, at times, he has adopted a scolding tone in speaking to young black men.

“Nobody cares how tough your upbringing was,” Obama told the new graduates at Morehouse. “Nobody cares if you suffered some discrimination. And moreover, you have to remember that whatever you’ve gone through, it pales in comparison to the hardships previous generations endured, and they overcame.”

Administration officials said Obama will seek to connect the progress of the past 50 years with the work that must be done over the next 50. But there will probably be only a few specific policy prescriptions mixed into the longer story he will tell about America and race.

Alan B. Williams, a Democratic state lawmaker from Florida who attended the White House meeting last month on voting rights, said the president made clear “the resolve that he has to ensure that the Voting Rights Act is reauthorized” following a U.S. Supreme Court ruling in June that invalidated a key part of the law.

The issue is one of the most direct political lines connecting King’s speech to a concern of Obama’s — threats to voting access.

Williams was born seven years after King’s assassination. He learned the “I Have a Dream” speech in first grade, eventually framing a copy of it along with a picture of himself and his sister. He shares it today with his teenage children.

At the 2004 Democratic National Convention, Williams met Obama, then a young state senator in Illinois, who would deliver a post-partisan appeal that would transform him into a national figure.

Four years later, Obama was elected president. And Williams, inspired to seek public office himself, won a seat in the Florida House after a career as a business consultant. He has gotten to know Obama a little since then.

“He has his voice — given to him by his mother, by his grandparents and also now by Michelle, the first lady,” Williams said. “The president must pick and choose when he comes out to speak on issues of race. But I can tell you, he does not allow anyone to put him in a box.”

Over the past few days, Williams and his children have been discussing King’s speech and its relevance today, especially in light of the nation’s first black president.

“Part of the dream has been realized, parts are being fulfilled and parts are evolving,” Williams said. “But it’s important to recall, and to this president, that the ‘I Have a Dream’ speech is not just a charge to white Americans, or even just Americans, but to the world.”

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